39835-06-8Relevant academic research and scientific papers
[3 + 2]-Cycloaddition of Azaoxyallyl Cations with 1,2-Benzisoxazoles: A Rapid Entry to Oxazolines
Feng, Juan,Zhao, Ming,Lin, Xuanzi
, p. 9548 - 9560 (2019/08/26)
A novel and efficient [3 + 2] cycloaddition reaction of azaoxyallyl cations and 1,2-benzisoxazoles to give oxazoline derivatives has been developed. The transformation provides a rapid entry to functionalized oxazoline scaffolds under mild and transition-metal-free conditions, which will greatly expand the reaction types of heterocycle chemistry and pave the way for syntheses of bioactive compounds.
Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
Nimnual, Phongprapan,Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
supporting information, p. 8657 - 8667 (2015/09/15)
The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
